Top 20 Best Coaching Questions

If you’re asking only typical surface, to-do-list style coaching questions, you’re already being replaced by an AI chatbot. InnerLifeSkills Master Coaching has always been about far more than to-do-list coaching.

Yes, goal setting, action planning and accountability questions are always part of life, executive, business, wellness and every niche of coaching, but to succeed it’s critical to go beyond this.

Your clients will thank you.

First, let’s look at 20 typical coaching questions you should already know (that ChatGPT created in 3 seconds).

Then look at our top 20 InnerLifeSkills coaching questions, which help you offer far more than to-do-list coaching.

10 typical ChatGPT-created coaching questions

1. What do you want to achieve through coaching?
2. What are your goals for this session?
3. What are the biggest challenges you are currently facing?
4. What motivates you to work towards your goals?
5. What do you think is holding you back from achieving your goals?
6. What are your strengths, and how can you leverage them to achieve your goals?
7. What are your weaknesses, and how can you work on them to achieve your goals?
8. What resources do you need to achieve your goals?
9. What steps can you take to overcome obstacles?
10. What is your vision for your future?

Master coaching is all about asking the right questions, but it’s also about asking at the right time and in the right way.

That’s why this guide isn’t just a list of great questions to ask your clients. It’s also filled with helpful insight into how to ask and when. We want you to succeed and build an ethical, conscious coaching business.

What we can learn from the ICF Core Competencies about powerful coaching questions

The International Coaching Federation includes “evokes awareness” among the 8 Core Competencies, and questioning is central to it. Truly, what we ask our clients and how we ask it impacts every competency.

In my early career as a life and business coach, I learned that what we ask clients can backfire even with the best intentions.

If you’ve ever asked a perfectly good question expecting a client to reply with an “aha” clarity, but instead they close their arms, hearts and minds and shut down, then you know how important this is.

With three decades of coaching experience, an MCC credential, and the joy of mentoring natural coaches into skilful, inspiring Master Coaches, here’s what I’ve learned about asking coaching questions.

Your coaching questions have the power to direct your client’s attention to the surface or the depth, the past or the future, the problems or the solutions.

Because questioning skills are critical coaching skills, every coach should work to build their coaching question vocabulary beyond typical surface questions that even an AI app can ask.

How we ask is as important as what we ask.

Remember that the coaching question isn’t enough.

We also need to learn how to ask (tone, wording) and when (at what stage in the session).

Asking even a brilliant question too soon can shut down the flow of a conversation.

Think of some questions as belonging on the ground and others as belonging in the clouds. Some questions focus clients on practical, ground-level detail. Others lift clients to a broad, inspirational aerial viewpoint.

If you feel inspired and someone asks you a ground-level “how, when” question, it can feel harsh, like popping your idea balloon. It would feel just as odd if you were deep in practical detail and someone asked you a lofty aerial question.

• Master Coaches learn to work intuitively, slowly lifting perspectives off the ground with high-level questions, and gently bringing people back down when practical details need to be excavated.

• And a master coach never uses questions in a vacuum: weave your client’s own words in (reflective backtracking), and make sure the question belongs to that moment in the conversation.

#20 How could you possibly make that a reality?

Coaching tip: soften the edge of your questions. This is a fairly typical solution-focused “how” question, but notice the words “possibly” and “could”.

They soften the edge, which relaxes the mind enough to explore possible solutions. If we ask harshly, we won’t harvest good treasures from our questioning.

This one belongs closer to the ground, when you’re discussing the practicalities of making a goal real, so keep it to the middle or end of the session. It’s premature to ask too soon.

#19 What is one small step you could take in the next few days towards your dream?

Coaching tip: don’t mix grounded practical questions with inspiring ones. This is another grounded, solution-focused question.

What I love is the “one small step”, which makes it better than “What steps can you take?”

It belongs in the middle to end of the session, when it feels time to get into the nitty-gritty of action. Don’t mix it with higher-level inspirational questions, or it will feel disjointed.

#18 Who else will benefit from you achieving this?

Coaching tip: use deepened value questions to create engagement and buy-in. This is what InnerLifeSkills calls a deepened value question. It belongs near the beginning, but you can use it any time your client needs more motivation.

It helps them realise that more people than just themselves will benefit from their success, which can be highly motivating.

Part of our job is to inspire, but it’s more important to help clients motivate themselves.

#17 What other areas of your life will benefit from you achieving this goal?

Coaching tip: don’t only use your why questions to motivate. This is a second deepened value question. If you don’t find someone’s why, you can’t find their way.

Please don’t make the mistake of using your reason to motivate someone else. Excavate their best reason, their most inspiring purpose behind their goal, and you’ll have a way to motivate them.

#16 How will you know that you are there?

Coaching tip: clarify and get evidence about what someone means. It’s amazing how often we assume we understand what somebody says. If you asked 20 people whether they want to be happy, most would say yes, but what would they each mean by “happy”?

This is an evidence question, used when establishing a contract or excavating a goal. We want to know what will prove to someone that they’ve reached success.

Two ways to unpack meaning: “May I ask what you mean by…?” or “Tell me more about what you mean when you say…”.

#15 How can you keep yourself on track?

Coaching tip: get your client to keep themselves on track. Establishing goals is one thing, taking action is quite another. Many people fail to implement, and this is where coaching matters, because it keeps people moving forward.

Our role is often to be an accountability partner, which isn’t about policing or managing. This is a deepening commitment question.

Notice we ask clients to find their own best solutions to stay on track. We don’t take it on our shoulders, and we don’t tell them how.

#14 What truly motivates you?

Coaching tip: find out what motivates your client. This lovely short question can open up a wonderful discussion. Clarifying what truly motivates us is an excavation into our core values. It belongs at the beginning of a session because it’s inspirational in nature.

The ICF encourages short, succinct questions, because long or stacked questions confuse clients. Can you feel how a simple “What truly motivates you?” is far better than a rambling version?

#13 Just suppose there were a few possible solutions; what 3 come to mind first?

Coaching tip: make your questions exploratory and experimental. If we ask too directly, like “What is the solution?”, we can pressure the client into surface answers or “I don’t know”. By asking for just a few “possible” solutions that simply “come to mind”, we make the conversation exploratory and low risk.

This invites innovation, intuition and creativity. The ICF distinguishes an inquiry (usually a single question) from a full exploration (several related questions where you excavate deeper awareness).

I call exploration taking out a picnic basket on the scenic route. Knowing when to inquire and when to explore is a key to mastering levels of coaching.

#12 When I repeat your words, what happens to how your body feels?

Coaching tip: include somatic explorations to deepen your session. When students ask how to take a session deeper than a surface conversation, I always suggest somatic coaching exploration (soma means body).

It quickly takes a session to new depths, though it’s not always easy to facilitate.

Here’s an example:

Client: “I’m inspired to let go of my self-doubt so I can finally step up and into my power.”
Coach: “If I repeat your words, I’d like to know how they land. What happens in your body when I say, I can finally step up and step into my power?”
Client: “I feel stronger.”
Coach: “You feel stronger. And what happens to your body posture when you step up and step into your power?”
Client: “My head lifts.”
Coach: “And what else? Take your time. If it helps, breathe in your words, step up and into your power.”
Client: “My shoulders relax. I feel like I can breathe deeper. I notice my feet connected to the ground.”

Example coaching session demonstration

As you can tell, the session has gone to a wonderful, deeper space. Imagine if the coach had missed this opportunity to explore the insight somatically.

#11 If you take a moment to imagine yourself already living the dream, how does that feel?

Coaching tip: help your client imagine their success, then plan from that perspective. This is like a condensed version of the NLP “as if” frame.

The theory is that the mind finds solutions more easily when it imagines already being in the reality of the goal. Instead of standing on one cliff wondering how to reach the far one, we imagine already being at the goal and ask the mind for the solutions we took in hindsight.

This is also called backward planning, and you can add somatic exploration for even more depth.

#10 May I challenge you here? You say you want this, but your tone seems unsure; what are your thoughts?

Coaching tip: ask permission to give feedback and challenge your client. If you sense your client is saying one thing but feeling another, or you have an intuition to stretch them, this can help. As coaches, we ask permission to challenge.

Ask this slowly, with established rapport and trust, most likely during a deeper exploratory part of the session.

Notice I add “I could be wrong”, which makes space for discussion and positions your feedback as an opinion, not a fact. This aligns with the ICF competencies.

#9 How can you best support yourself right now?

Coaching tip: help your client to help themselves. This is a good response if your client is feeling vulnerable or expressing difficult emotions. As coaches, we help people help themselves, we don’t carry their burdens.

We provide a safe, neutral, non-judgemental space and ask powerful questions so they discover their own best solutions. Give them a lot of space and don’t rush them, especially if they’re vulnerable.

The ICF asks us to neither dismiss nor disrespect a client’s beliefs, feelings or values.

Coaching is different from therapy, but when a client is vulnerable we don’t minimise their feelings, we make space to show we care.

#8 Even if the worst happened, what is still true that is important to you?

Coaching tip: find what is still true to neutralise a client’s fear. This comes from the InnerLifeSkills Personal Power short certification course and a process called “equal to future outcomes”.

I love it for neutralising our fears about the dreaded “what ifs” that keep us paralysed. The intention is to help the client find something that cannot be taken from a feared future.

When marking professional and master level assessments, we listen for evidence of the coach exploring the client’s what and who (in ICF language).

If you focus only on the practical to-do-list, you miss the inner work. By finding what is still true for a client, you uncover their values.

#7 Imagine you have that, completely and totally. What does it give you inside that is even more important?

Coaching tip: excavate your client’s core values. This question can be repeated again and again to help the client go deeper through layers of values until they strike the treasure of a core value. A core value is central to a person, a very significant aspect of themselves.

In an InnerLifeSkills process called the Kite, we use a client’s core value to transform an inner obstacle.

Here’s an example:

Client: “If I reach this goal, I will feel relief.”
Coach: “Imagine you had total and complete relief. Feel that for a moment. What does relief give you inside that’s even more important?”
Client: “Peace.”
Coach: “Now imagine total and complete peace. Breathe that in. With peace, what do you have inside that is even more important than peace?”
Client: “I feel free. I know I am enough.”
Coach: “You feel free. You know you are enough.”

Extract from a coaching session

#6 Imagine yourself a few years in the future; what advice would your future self give you today?

Coaching tip: get your client to give themselves good advice. This fun, easy question can open up a whole discussion and unearth valuable solutions.

Some of my graduate coaches have even turned it into an exercise, where clients write themselves letters from their future successful selves. What a wonderful way to help someone give themselves good advice.

#5 Just suppose that feeling was trying to give you something positive; what would it be?

Coaching tip: excavate a positive intention behind an inner obstacle. This is my number 5 because it comes from one of our most popular and powerful InnerLifeSkills processes, the InnerLifeSkills Kite, taught in our accredited Master Coach program.

It helps excavate the positive intention behind even destructive or limiting behaviours. Once we have that good reason behind the bad behaviour, we can leverage it to transform the behaviour. Ask it skilfully, with much rapport and trust.

#4 Why does this matter to you?

Coaching tip: help people discover and clarify meaning. This is a simple question, but it’s in the top 5 for a reason. Finding someone’s why is the key to their inspiration and motivation. Don’t assume your why will motivate your client.

Take the time to find theirs. Ask with a tone of curiosity, or add “I’m curious…”. And don’t assume people already know the answer. By asking, we help people discover and clarify what is only whispering inside them.

Now for my top 3 life coaching questions

#3 If you were guaranteed success, what would you try?

Coaching tip: create an inspiring vision for your client. This broad, sweeping, inspiring question deserves time and space. Don’t ask it in a quick, flippant way.

Reserve it for early in the session, when you want to lift the client to an aerial view, see the bigger picture, and create a vision.

#2 If you were totally free, who would you be?

Coaching tip: invite self-exploration into your coaching. One of my most inspiring dreams is to help others be free, free of the binding ignorance that restricts us. That’s why this is my second favourite question. It deserves time and space.

Don’t ask it quickly.

Reserve it for when your connection with the client is good and it feels right to open this line of self-inquiry. Don’t rush their answers.

Let them discover the many possibilities that can arise.

#1 What is the deeper truth?

Coaching tip: look for deeper truth. This is my favourite question. It’s the one I’ve used for over 20 years in self-coaching, meditation and contemplation when seeking inner wisdom.

I reserve it for that special moment when it’s time to let the truth illuminate and free someone’s mind. This isn’t a question you ask without deep reverence and respect.

To ask it well, hold a safe space, use silence, and stay in what the ICF calls coach presence: professional, caring, and without a personal agenda. Be egoless, neutral and non-judgemental.

If you don’t ask it properly, the client’s surface mind may answer “I don’t know”, or they won’t understand the question. But asked while seeking deep wisdom, it can be powerfully transformative.

Every time I’ve asked myself this question, adding my intuition to go deeper than my surface mind, I’ve found treasures that were often life-changing.

Every moment in our lives offers us the chance to look at the surface or to find the deeper truth.

The truth does set us free. Looking for it, and being willing to challenge anything less, takes courage. That is why this is my most prized and valued question.

Go beyond to-do-list coaching

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